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Title: Dissipative Assembly of Macrocycles Comprising Multiple Transient Bonds

Journal Article · · Angewandte Chemie (International Edition)

Dissipative assembly has great potential for the creation of new adaptive chemical systems. However, while molecular assembly at equilibrium is routinely used to prepare complex architectures from polyfunctional monomers, species formed out of equilibrium have, to this point, been structurally very simple. In most examples the fuel simply effects the formation of a single short-lived covalent bond. Here in this paper, we show that chemical fuels can assemble bifunctional components into macrocycles containing multiple transient bonds. Specifically, dicarboxylic acids give aqueous dianhydride macrocycles on treatment with a carbodiimide. The macrocycles are assembled efficiently as a consequence of both fuel-dependent and fuel-independent mechanisms; they undergo slower decomposition, building up as the fuel recycles the components, and are a favored product of the dynamic exchange of the anhydride bonds. These results create new possibilities for generating structurally sophisticated out-of-equilibrium species.

Research Organization:
Miami Univ., Oxford, OH (United States)
Sponsoring Organization:
USDOE Office of Science (SC), Basic Energy Sciences (BES)
Grant/Contract Number:
SC0018645
OSTI ID:
1657232
Alternate ID(s):
OSTI ID: 1631771
Journal Information:
Angewandte Chemie (International Edition), Vol. 59, Issue 33; ISSN 1433-7851
Publisher:
WileyCopyright Statement
Country of Publication:
United States
Language:
English
Citation Metrics:
Cited by: 34 works
Citation information provided by
Web of Science

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